N³-benzoyl-2',3'-O-isopropylidene uridine | 423769-51-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: N³-benzoyl-2',3'-O-isopropylidene uridine
• 英文别名: 3-N-benzoyl-2',3'-O-isopropylidene-uridine；3-N-benzoyl-2',3'-O-isopropylideneuridine；N3-benzoyl-2'3'-O-isopropylidene uridine；1-[(3aR,4R,6R,6aR)-6-(hydroxymethyl)-2,2-dimethyl-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxol-4-yl]-3-benzoylpyrimidine-2,4-dione
• CAS: 423769-51-1
• 化学式: C₁₉H₂₀N₂O₇
• 分子量: 388.377
• InChiKey: QHTCUCOSYNGUCL-DNNBLBMLSA-N

物化性质

• 沸点：
  551.5±60.0 °C(Predicted)
• 密度：
  1.394±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  28
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  106
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  4-O-Acetyl-3,6-di-O-benzyl-D-glucal 、 N³-benzoyl-2',3'-O-isopropylidene uridine 在 triphenylphosphine-hydrogen bromide 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以58%的产率得到
  参考文献：
  名称：

  Adducts of uridine and glycals as potential substrates for glycosyltransferases

  摘要：

  We report on the synthesis of 2-deoxyglycosyl derivatives of uridine as potential donor substrates for glycosyltransferases. The totally stereoselective synthesis is accomplished by two sequential addition reactions of uridine derivatives to glycals promoted by triphenylphosphine-hydrogen bromide. (c) 2007 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.bioorg.2007.07.001
• 作为产物：
  描述：

  N³,3',5'-O-tribenzoyl thymidine 在 吡啶 、 sodium hydroxide 、 三乙胺 、 苯甲醇 作用下， 以 二氯甲烷 为溶剂， 反应 39.0h， 生成 N³-benzoyl-2',3'-O-isopropylidene uridine
  参考文献：
  名称：

  合成N-苯甲酰化尿苷和胸苷衍生物的新方法；N-脱苯甲酰化的简便方法。

  摘要：

  已经开发了一种通过2'，3'-O-异亚丙基尿苷的一步选择性N-苯甲酰化合成N-苯甲酰基-2'，3'-O-异亚丙基尿苷的改进方法。还描述了通过初始的三苯甲酰化，然后选择性地水解苯甲酸酯来合成N-苯甲酰基胸苷的有效合成途径。N-苯甲酰化胸苷和尿苷衍生物的N-苯甲酰化可以在中性条件下通过与苄醇一起加热而方便地进行。

  DOI：

  10.1016/s0008-6215(01)00325-1

文献信息

• 5-Amino-2-pyridyl 1-thioglycosides in synthesis of analogs of glycosyltransferases substrates
  作者：Gabriela Pastuch-Gawolek、Tadeusz Bieg、Wieslaw Szeja、Jakub Flasz

  DOI：10.1016/j.bioorg.2009.04.002

  日期：2009.6

  We present the synthesis of 1-thioglycosyl derivatives of uridine. which were designed to act as potential donor substrates for glycosyltransferases. We constructed such analogs using 5-amino-2-pyridyl 1-thioglycosides as glycosyl units which were connected to uridine via succinic linker. For preparation of the amide bonds we applied different condensation procedures. (C) 2009 Elsevier Inc. All rights reserved.
• Development of O–H insertion for the attachment of phosphonates to nucleosides; synthesis of α-carboxy phosphononucleosides
  作者：Isabelle Hladezuk、Veronique Chastagner、Stuart G. Collins、Stephen J. Plunkett、Alan Ford、Sebastien Debarge、Anita R. Maguire

  DOI：10.1016/j.tet.2011.12.077

  日期：2012.2

  Development of rhodium catalysed O-H insertion reactions employing alpha-diazophosphonates with appropriately protected adenosine, uridine and thymidine derivatives is described. This synthetic methodology leads, following deprotection, to novel phosphononucleoside derivatives bearing a carboxylic acid moiety adjacent to the phosphonate. Protection strategies are critical to the success of the key O-H insertion. There are two important aspects: avoiding competing insertion pathways or catalyst poisoning, and being able to achieve deprotection without degradation of the phosphononucleosides. (C) 2012 Elsevier Ltd. All rights reserved.
• Adducts of uridine and glycals as potential substrates for glycosyltransferases
  作者：Ilona Wandzik、Tadeusz Bieg

  DOI：10.1016/j.bioorg.2007.07.001

  日期：2007.10

  We report on the synthesis of 2-deoxyglycosyl derivatives of uridine as potential donor substrates for glycosyltransferases. The totally stereoselective synthesis is accomplished by two sequential addition reactions of uridine derivatives to glycals promoted by triphenylphosphine-hydrogen bromide. (c) 2007 Elsevier Inc. All rights reserved.
• New methods for the synthesis of N-benzoylated uridine and thymidine derivatives; a convenient method for N-debenzoylation
  作者：Anita R. Maguire、Isabelle Hladezuk、Alan Ford

  DOI：10.1016/s0008-6215(01)00325-1

  日期：2002.2

  procedure for the synthesis of N-benzoyl-2',3'-O-isopropylidene uridine via one-step selective N-benzoylation of 2',3' -O-isopropylidene uridine has been developed. An efficient synthetic route to N-benzoyl thymidine via initial tribenzoylation, followed by selective hydrolysis of the benzoates is also described. De-N-benzoylation of N-benzoylated thymidine and uridine derivatives can be conveniently

  已经开发了一种通过2'，3'-O-异亚丙基尿苷的一步选择性N-苯甲酰化合成N-苯甲酰基-2'，3'-O-异亚丙基尿苷的改进方法。还描述了通过初始的三苯甲酰化，然后选择性地水解苯甲酸酯来合成N-苯甲酰基胸苷的有效合成途径。N-苯甲酰化胸苷和尿苷衍生物的N-苯甲酰化可以在中性条件下通过与苄醇一起加热而方便地进行。